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RESEARCH ARTICLE
Contents Vol 70(4)

Singlet Photoreactivity of 3-Methyl-2-phenyl-2H-azirine

Geethika K. Weragoda A , Anushree Das A , Sujan K. Sarkar A , H. Dushanee M. Sriyarathne A , Xiaoming Zhang A , Bruce S. Ault A and Anna D. Gudmundsdottir A B
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, University of Cincinnati, PO Box 210172, Cincinnati, OH 45221-0172, USA.

B Corresponding author. Email: Anna.Gudmundsdottir@uc.edu

Australian Journal of Chemistry 70(4) 413-420 https://doi.org/10.1071/CH16604
Submitted: 26 October 2016  Accepted: 2 February 2017   Published: 2 March 2017

Abstract

Irradiation of 3-methyl-2-phenyl-2H-azirine (1) at 254 nm in argon matrices results in ylide 6. Similarly, laser flash photolysis (λ = 266 nm) of azirine 1 in acetonitrile yields ylide 6, which has a transient absorption with λmax at ~340 nm and a lifetime of 14 μs. Density functional theory calculations were preformed to support the characterisation of ylide 6 in solution and argon matrices. Irradiation of azirine 1 above 300 nm has previously been reported (J. Org. Chem. 2014, 79, 653) to yield triplet vinylnitrene in solution and ketenimine in cryogenic argon matrices. Thus, the photochemistry of azirine 1 is dependent on the irradiation wavelength.


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